Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH3:12])[CH:6]=[C:5]2[C:13]#[N:14].[S:15]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16]1.[F-].[Cs+]>C([O-])(O)=O.[Na+].Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:11]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:17]3[CH:18]=[CH:19][S:15][CH:16]=3)=[CH:10][CH:9]=2)[C:5]([C:13]#[N:14])=[CH:6]1)[CH3:12]A tube was charged with a mixture of 5-bromo-1-ethyl-1H-indole-3-carbonitrile (100 mg, 0.40 mmol), thiophene-3-boronic acid (72 mg, 0.56 mmol), PdCl2(PPh3)2 (11 mg, 0.016 mmol) and CsF (152 mg, 1 mmol) and then alternately evacuated and filled with nitrogen (3×) and diluted with dimethoxyethane (3 mL) and then heated to 90° C. for 19 h. After cooling, the crude reaction mixture was diluted with saturated NaHCO3 and extracted with EtOAc (2×). The combined organic phases were washed with saturated NaCl and dried and concentrated. Flash chromatography over silica gel (CH2Cl2/hexanes, 40/60) gave 25 mg (25%) of 1-ethyl-5-thiophen-3-yl-1H-indole-3-carbonitrile as a white solid.
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